Dithienylcyclopentene-functionalised subphthalocyaninatoboron complexes: photochromism, luminescence modulation and formation of self-assembled monolayers on gold

Citation

Weidner, Tobias; Baio, Joe E.; Seibel, Johannes; & Siemeling, Ulrich (2012). Dithienylcyclopentene-functionalised subphthalocyaninatoboron complexes: photochromism, luminescence modulation and formation of self-assembled monolayers on gold. Dalton transactions (Cambridge, England: 2003), 41(5), 1553-1561.

Abstract

Subphthalocyaninatoboron (SubPc) complexes bearing six peripheral n-dodecylthio substituents and an apical photochromic dithienylperfluorocyclopentene unit were prepared. The photoinduced isomerisation of the apical substituent from the open to the ring-closed form significantly influences the photoluminescence of the covalently attached SubPc unit, which is more efficiently quenched by the ring-closed form. Films on gold were fabricated from these multifunctional conjugates and characterised by near-edge X-ray absorption fine structure (NEXAFS) and X-ray photoelectron spectroscopy (XPS). The results are in accord with the formation of self-assembled monolayers based on dome-shaped SubPc-based anchor groups. Their chemisorption is primarily due to the peripheral n-dodecylthio substituents, giving rise to covalently attached thiolate as well as coordinatively bound thioether units, whose alkyl chains are in an almost parallel orientation to the surface.

Keyword(s)

Boron Compounds
Cyclopentanes
gold
Indoles
Luminescence
Oxidation-Reduction
Photochemical Processes
Photoelectron Spectroscopy
Spectrophotometry, Ultraviolet

Reference Type

Journal Article

Secondary Title

Dalton transactions (Cambridge, England: 2003)

Author(s)

Weidner, Tobias
Baio, Joe E.
Seibel, Johannes
Siemeling, Ulrich

Year Published

2012

Date Published

1328572800

Volume Number

41

Issue Number

5

Pages

1553-1561

ISSN/ISBN

1477-9234

DOI

Dithienylcyclopentene-functionalised subphthalocyaninatoboron complexes10.1039/c1dt11644d